DESCRIPTION: (Principal Investigator's) Due to the "handedness" of the molecules of life, the development of efficient methods for stereoselective organic synthesis is essential to the expeditious discovery of new therapeutic compounds. This research program focuses on the development of enantioselective nucleophilic catalysts. Because nucleophiles catalyze an enormous array of useful reactions, work in this area provides the opportunity to develop a catalyst (or a small family of catalysts) that will effect a wide range of processes with high levels of enantioselectivity. This investigation is comprised of three areas of research: (1) The development of syntheses of planar-chiral pi complexes of heterocycles with transition metals; (2) The study of the capacity of these planar-chiral complexes to serve as nucleophilic catalysts for a wide array of reactions; (3) The development of enantioselective processes catalyzed by enantiopure planar-chiral pi complexes. It is anticipated that useful new methods for stereoselective organic synthesis will emerge from this investigation.